Another great variant of the casual look is the combination of the simple gray coat topping a sassy tight fitting dress and flat shoes or options on heels. Or else, you can combine a strict skirt with a minimalistic jacket or a blouse, or just spice up the look with a leather jacket, finishing all off with stilettos or just high heels. Multi-layered and complicated ensembles are the best way to create ideal casual combinations.
How to actually do it: "Don't give people too many things to look at all at once," says Halbreich. "If you're wearing a low-cut dress, focus on the cleavage—you don't also need bare arms and legs." The concept applies to fit as well: A body-hugging dress is better with a more sensible neckline and hem, whereas a skirt that hits a few inches above the knee won't raise eyebrows if it's flared rather than tight.
How to actually do it: "Figure out your go-to, foolproof looks," says designer Nanette Lepore, then seek out variations on that theme. Stumped? Picture the outfits that you feel most comfortable in. Or ask people close to you what you look best in. Once you've zeroed in on what works, find different takes. "I gravitate toward jackets, so I'll do a bomber style, then a silk version, or a denim jacket with leather sleeves," says Minkoff. "Whenever you feel the need to talk yourself into things, that's a red flag that you shouldn't buy them," says Minkoff. If you have doubts in the dressing room, it may help to take a photo of yourself in the item, suggests Aerin Lauder, the founder and creative director of the lifestyle brand Aerin. "It's much more accurate than looking in the mirror."
×